John McKindlay served his apprenticeship as a clerk with Cunningham and Reid, West Indies traders in Glasgow and Greenock. In 1777 he established himself in Montreal, and the following year he invested £830 in the fur trade, a small sum compared with the largest that year of about £24,000, put up by James McGill*; ten years later McKindlay invested £4,550, the fifth largest amount advanced by an individual. He had already become one of the most important suppliers to the northwest trade by the early 1780s. Among his customers was Jean-Étienne Waddens*, and after Waddens was murdered in 1782 it was McKindlay who deposited a list of the trader’s effects with a Montreal notary. McKindlay also stood security for traders, who needed guarantors of their good conduct in the Indian country in order to obtain a trading licence from government.

For a time, around 1784, McKindlay was in partnership with Étienne Dumeyniou, a French merchant in Montreal, and when Dumeyniou retired McKindlay took their clerk, William Parker, into partnership. McKindlay was also a general trader on his own account, and he did well as an importer specializing in textiles and liquor, mostly from Scotland; he had good contacts in Greenock, notably Allan, Kerr and Company, a principal Scottish firm in the trade to the colony. He was undoubtedly supplied from London by Robert Hunter, whose son Robert was hosted by McKindlay in Montreal in 1785. When Richard Dobie* mentioned to young Hunter that Montreal businessmen suffered much from fire, the latter noted “how well McKindlay bas provided against it. His goods were in excellent order and his warehouses very complete.” By the late 1780s a solid reputation enabled McKindlay to act as a curator of estates and business agent for merchants outside Montreal as he did for Adam Lymburner*, a relative, in a property seizure in 1795. In the same period his own need to have properties seized for non-payment of debts owed to him may have involved him in land speculation in Montreal. He sold wholesale to rural merchants in the Montreal district, and at L’Assomption, where he was the principal supplier, and in 1792 all his customers but one were indebted to him.

It was also to collect a debt that McKindlay had the seigneury of Lac-Matapédia, owned by the rural merchant Jean-Baptiste Raymond, sold at sheriff’s auction in 1797. When it was purchased by Patrick Langan, McKindlay acquired a one-third share, probably as payment of Raymond’s debt. His dealings with Raymond reflect McKindlay’s keen interest by the 1790s in the increasingly favourable prospects of Lower Canada as a grain-growing centre and a supplier of potash for markets in Britain and the West Indies. By 1795 he had begun to make large-scale purchases of those commodities, like his countryman and friend James Dunlop*. McKindlay employed agents to travel throughout the cultivated parts of the colony and buy up crops from country merchants, such as Raymond, and farmers. Among the agents were several young men, some of them his relations, brought out from Scotland on condition that they learn to speak French within a year. In 1796 McKindlay was negotiating with the Hôtel-Dieu of Montreal, either for the purchase of the sub-fief of Saint-Augustin or the lease of the farm there, but Bishop Jean-François Hubert* stopped the discussions.

McKindlay had probably achieved prosperity and a certain prominence by 1788, when he bought a two-storey stone house on Rue Notre-Dame. As a merchant he was led, like many of his colleagues, to become active in public affairs. From 1784 he signed numerous petitions for an elective assembly, which the merchants hoped to control in order to make the colony institutionally better adapted to commercial activity; when in 1792 elections were held to choose members of the first house of assembly, he was among some 20 of the city’s most prominent businessmen supporting the nominations of merchants James McGill, John Richardson, Joseph Frobisher*, and Alexander Auldjo in the city’s two electoral districts. In 1786–87 he had been on a committee of Montreal merchants which reported to the Legislative Council on the state of commerce in the colony. In 1790 he was elected a director of the Agriculture Society in Montreal, newly formed to render colonial agriculture more commercial through the introduction of advanced techniques of cultivation and animal husbandry, an objective close to McKindlay’s heart. The same year he took part in an unsuccessful campaign to secure the establishment of a custom-house at Montreal, and in November he was publicly thanked for his exertions by a group of his fellow merchants. In December 1802 he was elected by an assembly of businessmen to a committee charged with pressuring London fire insurance companies operating in the city to lower their premiums.

McKindlay was also involved in public matters not directly related to commerce: in 1788 he was appointed a justice of the peace, two years later he supported the establishment of a non-sectarian university in the colony [see Jean-François Hubert], and in 1794 he was given a commission of oyer and terminer and general jail delivery. A leading light in the Scotch Presbyterian Church, in July 1803 he signed a call to James Somerville* in preference to Robert Forrest as the replacement for the congregation’s disgraced minister, John Young.

In March 1799 McKindlay had sold his establishment on Rue Notre-Dame for £1,500. He moved into a larger commercial establishment clustered around a two-storey stone house on Rue Saint-Paul. In addition to continuing his other activities, by June 1799 he had moved into the timber trade. According to Lord Selkirk [Douglas*], the estimated value of McKindlay’s exports of all products in 1803 was £25,000, placing him among the city’s ten largest exporters. By early 1804, however, he appears to have run into financial difficulties, caused in part by defaulting debtors, all Canadians and possibly retailers whom he supplied. In April 1804 he borrowed some £2,300 from Richard Dobie. About the same time he sold his business and returned to Scotland, apparently giving his friend Samuel Gerrard* power of attorney to handle his affairs in Montreal. However, the sale must have been annulled, because in April 1806 the establishment on Rue Saint-Paul was seized by the sheriff at the suit of Adam Lymburner; at that time it covered an entire city block, bounded by Saint-Paul, Saint-Denis, Sainte-Thérèse, and Saint-Vincent streets, in the centre of Montreal, “with a large commodious Dwelling House, two small houses, vaults, cellars, stores, and out houses, . . . the whole . . . well adapted for carrying on an extensive business.” McKindlay apparently found the means to pay Lymburner, however, since the sale did not take place. In Scotland he lived for a time in considerable style in a mansion that he purchased at Cathkin Braes, on the outskirts of Glasgow, but by June 1806 he was established in Saltcoats. He acted as Dobie’s attorney and from 1805 as an executor of the wills of Dobie and Andrew McGill, James’s brother. In November 1811 he sold his Montreal business for £4,000 to Henderson, Armour and Company [see Robert Armour*].

Since at least 1796 McKindlay had been concentrating his efforts increasingly on land speculation in the Canadas. Between 1799 and 1826, but for the most part before 1806, he obtained numerous small grants in Upper Canada, totalling at least 14,000 acres scattered through 12 townships in the Ottawa and St Lawrence valleys. In the period 1809–11 he received several extensive grants in Hinchinbrook and Hemmingford townships, Lower Canada, and in 1814 Governor Sir George Prevost* granted him 3,775 acres in Godmanchester Township, which, by the system of township leaders and associates [see Samuel Gale] ay ultimately have brought him some 17,000 acres. He also bought land. On some of his properties he cut timber for export and fostered grain growing and dairy farming. He continued to promote new agricultural techniques in Lower Canada and encouraged the settlement of some of his lands by experienced immigrant farmers from Scotland and the north of England. On 12 Jan. 1822 McKindlay sold all his lands and land claims in the Canadas, except his share in the seigneury of Lac-Matapédia, to John Gray of Montreal for £2,107. The lands in Upper Canada, then totalling around 15,000 acres, were by far the more valuable since Gray paid £1,707 for them; most of the remaining lands, comprising some 12,275 acres, were in Lower Canada.

By 1818 McKindlay had prospered sufficiently to purchase another estate at Cathkin Braes, and he moved there permanently in 1823, occasionally revisiting Lower Canada to oversee his affairs in the province. In Scotland he showed as much interest in agricultural improvement as he had in Lower Canada and tenanted his farms with men who employed advanced techniques of cattle breeding and the growing of turnips and other root crops for animal feed. He was highly regarded as a progressive landowner in circles that promoted agricultural shows and exhibitions. He invested in Goal mines, shipping, and the timber trade with the Canadas. By the time of his death in 1833 he was considered a characteristic mercantile Scot who had done extremely well in the colonies.

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